Pest control agent/pf 1022-221

ABSTRACT

The present invention relates to the use of a 24-membered cyclodepsipeptide of the formula (I)  
                 
 
     for controlling animal pests in agriculture, forests and the protection of materials, and to pesticides comprising this depsipeptide.

[0001] The present invention relates to the use of a 24-memberedcyclodepsipeptide for controlling animal pests in agriculture, forestsand the protection of materials, and to pesticides comprising thisdepsipeptide.

[0002] Cyclic depsipeptides, and their preparation and use asparasiticides against helminths, nematodes and trematodes in animals(endoparasiticides) have already been the subject of numerouspublications.

[0003] Known is, for example, a cyclodepsipeptide with the name PF 1022Aand its action against endoparasites (EP-A 382 173 and EP-A 503 538).Further cyclic depsipeptides (cyclooctadepsipeptides: WO 98/55 469; WO98/43 965; WO 93/19 053; EP-A 634 408; WO 94/19 334; WO 95/07 272; EP-A626 375; EP-A 626 376; EP-A 664 297; EP 634 408; EP-A 718 298; WO 97/09331; cyclohexadepsipeptides: WO 93/25 543; WO 95/27 498; EP-A 658 551;cyclotetradepsipeptides: EP-A 664 297; dioxomorpholines: WO 96/38 165;JP 08 225 552) and open-chain depsipeptides (EP-A 657 171; EP-A 657 172;EP-A 657 173; WO 97/07 093) and their endoparasiticicidal action havebeen described.

[0004] Furthermore, it is already known that certain 24-memberedcyclodepsipeptides, for example bassianolide and PF1022A, haveinsecticidal activity against silkworms (cf. M. Kanaoka et al., Agric.Biol. Chem. 43 (5), 1979, pp. 1079-83; JP 05 271 013).

[0005] However, the insecticidal activity of these prior-art compoundsis, in particular at low application rates and concentrations, notentirely satisfactory in all areas of use.

[0006] The invention relates to a composition for controlling animalpests, characterized in that it comprises the compound of the formula(I)

[0007] The invention furthermore relates to the use of the compound ofthe formula (I) for controlling animal pests, in particular insects.

[0008] The cyclodepsipeptide of the formula (I) which can be usedaccording to the invention and its preparation are known from EP-A 634408 (WO 93/19 053) and EP-A 872 481 (WO 97/02 256).

[0009] Surprisingly, it has been found that the compound of the formula(I) is highly suitable for controlling animal pests in agriculture, inparticular in crop protection, forestry and the protection of materials.

[0010] With good plant tolerability and favourable homoiothermictoxicity, the active compound is suitable for controlling animal pests,in particular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene sector. It is active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

[0011] From the order of Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0012] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0013] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spec.

[0014] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0015] From the order of the Thysanura, for example, Lepisma saccharina.

[0016] From the order of the Collembola, for example, Onychiurusarmatus.

[0017] From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blatella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

[0018] From the order of the Dermaptera, for example, Forficulaauricularia.

[0019] From the order of the Isoptera, for example, Reticulitermes spp.

[0020] From the order of the Anoplura, for example, Pediculus humanuscorporis, Haematopinus spp. and Linognathus spp.

[0021] From the order of the Mallophaga, for example, Trichodectes spp.and Damalinea spp.

[0022] From the order of the Thysanoptera, for example, Hercinothripsfemoralis and Thrips tabaci.

[0023] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0024] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix,Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,Pseudococcus spp. and Psylla spp.

[0025] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp, Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

[0026] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrbynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

[0027] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0028] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

[0029] From the order of the Siphonaptera, for example, Xenopsyllacheopis and Ceratophyllus spp.

[0030] From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

[0031] From the order of the Acarina, for example, Acarus siro, Argasspp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis,Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommaspp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp.,Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. andTetranychus spp.

[0032] The phytoparasitic nematodes include Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp.,Xiphinema spp. and Trichodorus spp.

[0033] The active compound of the formula (I) which can be usedaccording to the invention is particularly distinguished by an excellentactivity against phytopathogenic pests, in particular againstlepidoptera such as the caterpillars of the owlet moth (Spodopterafrugiperda) and army worm (Heliothis virescens) larvae.

[0034] The active compound can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusting agents, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and very fine capsules in polymericsubstances.

[0035] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is liquid solventsand/or solid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

[0036] If the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes of methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as water.

[0037] As solid carriers there are suitable:

[0038] for example ammonium salts and ground natural minerals, such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates, as solid carriers for granulesthere are suitable: for example crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite and alsosynthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; as emulsifiers and/or foam-formers there are suitable: forexample non-ionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates andalso protein hydrolysates; as dispersing agents there are suitable: forexample lignin-sulphite waste liquors and methyl cellulose.

[0039] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0040] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0041] The formulations in general contain between 0.1 and 95 per centby weight of active compound, preferably between 0.5 and 90%.

[0042] The active compound according to the invention can be present inits commercially available formulations and in the use forms preparedfrom these formulations, as a mixture with other active compounds, suchas insecticides, attractants, sterilizing agents, bactericides,acaricides, nematicides, fungicides, growth-regulating substances orherbicides. The insecticides include, for example, phosphates,carbamates, carboxylates, chlorinated hydrocarbons, phenylureas andsubstances produced by microorganisms.

[0043] Examples of particularly advantageous mixture components are thefollowing compounds:

[0044] Fungicides:

[0045] 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxy-phenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyano-phenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino-[alpha-(o-tolyloxy)-o-tolyl]-acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

[0046] benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

[0047] calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

[0048] dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

[0049] edifenphos, epoxyconazole, ethirimol, etridiazole,

[0050] fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

[0051] guazatine,

[0052] hexachlorobenzene, hexaconazole, hymexazol,

[0053] imazalil, imibenconazole, iminoctadine, iprobenfos (IBP),iprodione, isoprothiolane,

[0054] kasugamycin, copper preparations such as: copper hydroxide,copper naphthenate, copper oxychloride, copper sulphate, copper oxide,oxine-copper and Bordeaux mixture,

[0055] mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax,myclobutanil,

[0056] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0057] ofurace, oxadixyl, oxamocarb, oxycarboxin,

[0058] pefurazoate, penconazole, pencycuron, phosdiphen, phthalide,pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz,procymidone, propamocarb, propiconazole, propineb, pyrazophos,pyrifenox, pyrimethanil, pyroquilon,

[0059] quintozene (PCNB),

[0060] sulphur and sulphur preparations,

[0061] tebucanozole, tecloftalam, tecnazene, tetraconazole,thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide,tricyclazole, tridemorph, triflumizole, triforine, triticonazole,

[0062] validamycin A, vinclozolin,

[0063] zineb, ziram.

[0064] Bactericides:

[0065] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0066] Insecticides/Acaricides/Nematicides:

[0067] abamectin, acephate, acetamiprid, acrinathrin, alanycarb,aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphosM, azocyclotin,

[0068]Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveriatenella, bendiocarb, benfuracarb, bensultap, benzoximate,betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

[0069] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cisperrnethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

[0070] deltamethrin, demeton M, demeton S, demeton-S-methyl, diacloden,diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoat,dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,

[0071] eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthoraspp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,etoxazole, etrimfos,

[0072] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

[0073] granulosis viruses,

[0074] halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,hydroprene,

[0075] imidacloprid, isazophos, isofenphos, isoxathion, ivermectin,

[0076] lambda-cyhalothrin, lufenuron,

[0077] malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

[0078] naled, nitenpyram, nithiazine, novaluron, nuclear polyhedrosisviruses,

[0079] omethoat, oxamyl, oxydemethon M,

[0080]Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoat, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb,pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur, prothiofos,prothoat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben,pyridathion, pyrimidifen, pyriproxyfen,

[0081] quinalphos,

[0082] ribavirin,

[0083] salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

[0084] tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiapronil, thiatriphos,thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin,tralocythrin, tralomethrin, triarathene, triazamate, triazophos,triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,

[0085] vamidothion, vaniliprole, Verticillium lecanii,

[0086] YI 5302,

[0087] zeta-cypermethrin, zolaprofos,

[0088](1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]2,2-dimethylcyclopropanecarboxylate,

[0089] (3-phenoxyphenyl)-methyl2,2,3,3-tetramethylcyclopropanecarboxylate,

[0090]1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

[0091] 2-(2-chloro-6-fluorophenyl)-4-[4-( 1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

[0092] 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

[0093] 2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0094] 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0095] 3-methylphenyl propylcarbamate

[0096] 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

[0097]4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

[0098]4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)-methoxy]-3(2H)-pyridazinone,

[0099]4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

[0100]Bacillus thuringiensis strain EG-2348,

[0101] [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

[0102] 2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl butanoate,

[0103][3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

[0104] dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

[0105] ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

[0106] N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

[0107]N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

[0108] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

[0109] N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

[0110] N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

[0111] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

[0112] It is also possible to admix other known active compounds, suchas herbicides, fertilizers and growth-regulating substances.

[0113] The active compound according to the invention can furthermore bepresent in its commercially available formulations and in the use formsprepared from these formulations, as a mixture with synergistic agents.Synergistic agents are compounds which increase the action of the activecompounds without it being necessary for the synergistic agent added tobe active itself.

[0114] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[0115] The compounds are employed in a customary manner appropriate forthe use forms.

[0116] When used against hygiene pests and pests of stored products, theactive compound has excellent residual action on wood and clay and alsogood stability to alkali on limed substrates.

[0117] Furthermore, it has been found that the compound of the formula(I) according to the invention has potent insecticidal action againstinsects which destroy industrial materials.

[0118] The following insects may be mentioned by way of example and asbeing preferred, but without any limitation:

[0119] Beetles, such as

[0120]Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex,Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus,Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Zyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

[0121] Dermapterans, such as

[0122]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerusaugur.

[0123] Termites, such as

[0124]Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Reticulitermes flavipes, Reticulitermes santonensis,Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsisnevadensis, Coptotermes formosanus.

[0125] Bristletails, such as Lepisma saccharina.

[0126] Industrial materials are to be understood as meaning, in thepresent context, non-live materials such as, preferably, syntheticmaterials, glues, sizes, paper and board, leather, wood and timberproducts, and paint.

[0127] The materials to be very particularly protected against attack byinsects are wood and timber products.

[0128] Wood and timber products which can be protected by thecomposition according to the invention or mixtures comprising such acomposition are to be understood as meaning, for example, constructiontimber, wooden beams, railway sleepers, bridge components, jetties,wooden vehicles, boxes, pallets, containers, telephone poles, woodlagging, windows and doors made of wood, plywood, particle board,joiner's articles, or wood products which, quite generally, are used inthe construction of houses or in joinery.

[0129] The active compounds can be used as such, in the form ofconcentrates or generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

[0130] The formulations mentioned can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if appropriate desiccants and UV stabilizers and, ifappropriate, colorants and pigments and other processing auxiliaries.

[0131] The insecticidal compositions or concentrates used for theprotection of wood and wooden materials comprise the active compoundaccording to the invention at a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

[0132] The amount of the compositions or concentrates employed dependson the species and the occurrence of the insects and on the medium. Theoptimum rate of application can be determined upon use in each case bytest series. However, in general, it suffices to employ 0.0001 to 20% byweight, preferably 0.001 to 10% by weight, of the active compound, basedon the material to be protected.

[0133] The solvent and/or diluent used is an organochemical solvent orsolvent mixture and/or an oily or oil-type organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water and, if appropriate, an emulsifierand/or wetting agent.

[0134] Organochemical solvents which are preferably employed are oily oroil-type solvents having an evaporation number of above 35 and aflashpoint of above 30° C., preferably above 45° C. Substances which areused as such oily and oil-type solvents which have low volatility andare insoluble in water are suitable mineral oils or their aromaticfractions, or mineral-oil-containing solvent mixtures, preferably whitespirit, petroleum and/or alkylbenzene.

[0135] Substances which are advantageously used are mineral oils with aboiling range of 170 to 220° C., white spirit with a boiling range of170 to 220° C., spindle oil with a boiling range of 250 to 350° C.,petroleum or aromatics of boiling range 160 to 280° C., essence ofturpentine and the like.

[0136] In a preferred embodiment, liquid aliphatic hydrocarbons with aboiling range of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

[0137] The organic oily or oil-type solvents of low volatility having anevaporation number of above 35 and a flashpoint of above 30° C.,preferably above 45° C., can be partially replaced by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flashpoint ofabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

[0138] In a preferred embodiment, part of the organochemical solvent orsolvent mixture is replaced by an aliphatic polar organochemical solventor solvent mixture. Substances which are preferably used are aliphaticorganochemical solvents having hydroxyl and/or ester and/or ethergroups, such as, for example, glycol ether, esters and the like.

[0139] The organochemical binders used within the scope of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se and can be diluted with water and/or are soluble ordispersible or emulsifiable in the organochemical solvents employed, inparticular binders composed of, or comprising, an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenol resin, hydrocarbon resin, such asindene/coumarone resin, silicone resin, drying vegetable and/or dryingoils and/or physically drying binders based on a natural and/orsynthetic resin.

[0140] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Up to 10% by weight ofbitumen or bituminous substances can also be used as binders. Inaddition, colorants, pigments, water repellents, odour-maskingsubstances and inhibitors or anticorrosives known per se and the likecan also be employed.

[0141] The composition or the concentrate preferably comprises, inaccordance with the invention, at least one alkyd resin or modifiedalkyd resin and/or a drying vegetable oil as the organochemical binder.Preferably used according to the invention are alkyd resins with an oilcontent of over 45% by weight, preferably 50 to 68% by weight.

[0142] All or some of the abovementioned binder can be replaced by afixative (mixture) or a plasticizer (mixture). These additives areintended to prevent volatilization of the active compounds andcrystallization or precipitation. They preferably replace 0.01 to 30% ofthe binder (based on 100% of binder employed).

[0143] The plasticizers are from the chemical classes of the phthalicesters, such as dibutyl phthalate, dioctyl phthalate or benzylbutylphthalate, the phosphoric esters, such as tributyl phosphate, the adipicesters, such as di-(2-ethylhexyl) adipate, the stearates, such as butylstearate or amyl stearate, the oleates, such as butyl oleate, glycerolethers or relatively high-molecular-weight glycol ethers, glycerolesters and p-toluene-sulphonic esters.

[0144] Fixatives are chemically based on polyvinyl alkyl ethers, suchas, for example, polyvinyl methyl ether, or ketones, such asbenzophenone or ethylene benzophenone.

[0145] Particularly suitable as a solvent or diluent is also water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

[0146] Particularly effective protection of wood is achieved bylarge-scale industrial impregnation processes, for example vacuum,double-vacuum or pressure processes.

[0147] If appropriate, the ready-to-use compositions can additionallycomprise one or more other insecticides and, if appropriate,additionally one or more fungicides.

[0148] Suitable additional components which may be admixed are,preferably, the insecticides and fungicides mentioned in WO 94/29 268.The compounds mentioned in that document are expressly part of thepresent application.

[0149] Very particularly preferred components which may be admixed areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorofluanide, tolylfluanide,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

EXAMPLES Example 1

[0150] Phaedon larvae test

[0151] Solvent: 3 parts by weight of dimethylformamide

[0152] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0153] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0154] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andpopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

[0155] After the desired period of time, the kill in % is determined.100% means that all beetle larvae have been killed; 0% means that noneof the beetle larvae have been killed.

[0156] At an active compound concentration of 1000 ppm, the compound ofthe formula (I) achieved a kill rate of 100%.

Example 2

[0157] Plutella test/symptomatology study

[0158] Solvent: Acetone

[0159] To prepare an advantgeous preparation of active compound, 10 mgof active compound are mixed with 1 ml of solvent.

[0160] 1 μl of the solution prepared in this manner is administered tocaterpillars of the diamond back moth (Plutella xylostella).

[0161] After the desired period of time, the kill in % is determined100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0162] At an active compound concentration of 10 μg/larva, the compoundof the formula (I) achieved a kill rate of 100%.

Example 3

[0163]Spodoptera frugiperda test

[0164] Solvent: 31 parts by weight of acetone

[0165] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0166] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0167] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andpopulated with caterpillars of the army worm (Spodoptera frugiperda)while the leaves are still moist.

[0168] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0169] At an active compound concentration of 1000 ppm, the compound ofthe formula (I) achieved a kill rate of 100%.

Example 4

[0170] Meloidogyne test

[0171] Solvent: 3 parts by weight of dimethylformamide

[0172] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0173] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0174] Vessels are filled with sand, a solution of the active compound,Meloidogyne incognita-egg larvae suspension and lettuce seeds. Thelettuice seeds germinate, and the small plants develop. On the roots,galls are formed.

[0175] After the desired period of time, the nematicidal action isdetermined in % by the formation of galls. 100% means that no galls havebeen found; 0% means that the number of galls on the treated plantscorresponds to that of the untreated control.

[0176] At an active compound concentration of 20 ppm, the compound ofthe formula (I) achieved an effect of 98%.

1. Composition for controlling animal pests, characterized in that itcomprises the compound of the formula (I)


2. Use of the compound of the formula (I) according to claim 1 forcontrolling animal pests.
 3. Use of the compound of the formula (I) forcontrolling insects.